[ CAS No. 116308-35-1 ] {[proInfo.proName]}

Name: 116308-35-1|2-(Trifluoromethyl)nicotinaldehyde|95%
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Quality Control of [ 116308-35-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 116308-35-1 ]

Product Details of [ 116308-35-1 ]

CAS No. :	116308-35-1	MDL No. :	MFCD08234912
Formula :	C₇H₄F₃NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	COMFXXABDQGVSV-UHFFFAOYSA-N
M.W :	175.11	Pubchem ID :	14761475
Synonyms :

Calculated chemistry of [ 116308-35-1 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.63
TPSA :	29.96 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.32
Log Po/w (XLOGP3) :	1.23
Log Po/w (WLOGP) :	3.07
Log Po/w (MLOGP) :	0.89
Log Po/w (SILICOS-IT) :	2.5
Consensus Log Po/w :	1.8

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.94
Solubility :	2.02 mg/ml ; 0.0115 mol/l
Class :	Very soluble
Log S (Ali) :	-1.46
Solubility :	6.12 mg/ml ; 0.0349 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.86
Solubility :	0.244 mg/ml ; 0.00139 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.34

Safety of [ 116308-35-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 116308-35-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 116308-35-1 ]
Downstream synthetic route of [ 116308-35-1 ]

[ 116308-35-1 ] Synthesis Path-Upstream 1~8

1
[ 131747-57-4 ]
[ 116308-35-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	With manganese(IV) oxide In dichloromethane for 4 h; Reflux	(2-trifluoromethyl-pyridin-3-yl)methanol (0.05g, 0.28 mmol) was dissolved in anhydrous dichloromethane (10 mL). To this was added manganese dioxide (0.7 g,8.0 mmol). The mixture was stirred atreflux for 4 hours. The mixture was then cooled to room temperature and filtered through Celite. The resulting filtrate was concentrated on a rotary evaporator to yield the desired product as a yellow oil (0.035 g, 71percent yield) which was used without further purification. ¹H-NMR (400Mz, CDCl₃) δ 10.40 (s, 1H), 8.83 (d, J = 4.7 Hz, 1H), 8.37 (d, J = 8.0 Hz, 1H), 7.63 (dd, J = 8.0 and 4.7 Hz, 1H). MS(ESI+): m/z (M+H)⁺ = 176.

Reference： [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5352 - 5359
[3] Synthesis, 2005, # 16, p. 2751 - 2757
[4] Patent: WO2012/87519, 2012, A1, . Location in patent: Page/Page column 123

2
[ 128071-75-0 ]
[ 116308-35-1 ]

Reference： [1] Organic Letters, 2014, vol. 16, # 6, p. 1744 - 1747

3
[ 128071-75-0 ]
[ 77152-08-0 ]
[ 116308-35-1 ]

Reference： [1] Journal of Organic Chemistry, 2013, vol. 78, # 22, p. 11126 - 11146

4
[ 208517-35-5 ]
[ 116308-35-1 ]

Reference： [1] Synthesis, 2005, # 16, p. 2751 - 2757
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5352 - 5359

5
[ 131747-43-8 ]
[ 116308-35-1 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[2] Patent: WO2012/87519, 2012, A1,

6
[ 1603-40-3 ]
[ 116308-35-1 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458

7
[ 3430-17-9 ]
[ 116308-35-1 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458

8
[ 1620-78-6 ]
[ 116308-35-1 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458

[ 116308-35-1 ] Synthesis Path-Downstream 1~33

1
[ 131747-57-4 ]
[ 116308-35-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	With manganese(IV) oxide; In dichloromethane; for 4h;Reflux;	(2-trifluoromethyl-pyridin-3-yl)methanol (0.05g, 0.28 mmol) was dissolved in anhydrous dichloromethane (10 mL). To this was added manganese dioxide (0.7 g,8.0 mmol). The mixture was stirred atreflux for 4 hours. The mixture was then cooled to room temperature and filtered through Celite. The resulting filtrate was concentrated on a rotary evaporator to yield the desired product as a yellow oil (0.035 g, 71% yield) which was used without further purification. 1H-NMR (400Mz, CDCl3) delta 10.40 (s, 1H), 8.83 (d, J = 4.7 Hz, 1H), 8.37 (d, J = 8.0 Hz, 1H), 7.63 (dd, J = 8.0 and 4.7 Hz, 1H). MS(ESI+): m/z (M+H)+ = 176.
	With manganese(IV) oxide; In dichloromethane; at 50℃; for 72h;	Mn02 (6.10 g, 70.6 mmol) was added portionwise to a solution of the above (2-(trifluoromethyl)pyridin-3-yl)methanol (I-29A) (2.5 g, 14.1 mmol) in dry dichloromethane (300 mL), and the resulting suspension was heated to 50C for 72 hours. After this time the mixture was filtered through celite and the filtrate concentrate in vacuo to afford a brown oil. This crude oil was purified by silica gel chromatography using a gradient of 0-30% ethyl acetate-hexane to furnish 2-(trifluoromethyl)nicotinaldehyde (I-29B) as clear oil. 1H-NMR (400 MHz, CDC13) delta 10.4 (m, 1H), 8.89 (dd, J = 4.8 and 1.2 Hz, 1H), 8.45 (dd, J = 8.0, and 1.6 Hz, 1H), 7.70 (dd, J = 8.0 and 4.8 Hz, 1H). MS m/z 176.0 (M + 1).

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 2446 - 2458
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5352 - 5359
[3]Synthesis,2005,p. 2751 - 2757
[4]Patent: WO2012/87519,2012,A1 .Location in patent: Page/Page column 123

2
[ 116308-35-1 ]
[ 116308-57-7 ]
[ 21731-17-9 ]
[ 116308-45-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 91 - 99

3
[ 116308-35-1 ]
[ 116308-37-3 ]
[ 21731-17-9 ]
[ 116308-49-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 91 - 99

4
[ 116308-35-1 ]
[ 116308-41-9 ]
[ 21731-17-9 ]
[ 116308-53-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 91 - 99

5
[ 54527-68-3 ]
[ 116308-35-1 ]
[ 14205-39-1 ]
[ 131747-84-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 2446 - 2458

6
[ 1816-92-8 ]
[ 116308-35-1 ]
[ 871583-03-8 ]

Reference： [1]Synthesis,2005,p. 2751 - 2757

7
[ 116308-35-1 ]
methyl 4-(trifluoromethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate [ No CAS ]

Reference： [1]Synthesis,2005,p. 2751 - 2757

8
[ 208517-35-5 ]
[ 116308-35-1 ]

Reference： [1]Synthesis,2005,p. 2751 - 2757
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5352 - 5359

9
[ 1603-40-3 ]
[ 116308-35-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 2446 - 2458

10
[ 3430-17-9 ]
[ 116308-35-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 2446 - 2458

11
[ 1620-78-6 ]
[ 116308-35-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 2446 - 2458

12
[ 116308-35-1 ]
[ 108337-84-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 2446 - 2458

13
[ 131747-43-8 ]
[ 116308-35-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 2446 - 2458
[2]Patent: WO2012/87519,2012,A1

14
[ 128071-75-0 ]
[ 77152-08-0 ]
[ 116308-35-1 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11126 - 11146

15
(1,10-phenanthroline)(trifluoromethyl)copper(I) [ No CAS ]
[ 128071-75-0 ]
[ 116308-35-1 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1744 - 1747

16
[ 579-74-8 ]
[ 116308-35-1 ]
(E)-1-(2-methoxyphenyl)-3-(2-(trifluoromethyl)pyridine-3-yl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%		A solution of lithium hydroxide (0.8 mg, 0.03 mmol) and 2'-methoxyacetophenone (26 mg, 0.157 mmol) in absolute methanol (1.5 mL) was stirred at room temperature for 15 min. To the resulting mixture was added a solution of <strong>[116308-35-1]2-(trifluoromethyl)-3-pyridinecarboxaldehyde</strong> (6a, 28 mg, 0.16 mmol) in absolute methanol (15 mL). The reaction was stirred overnight at room temperature (approx. 18 h). The reaction was then concentrated on a rotary evaporator and the resulting oily residue purified by chromatography on silica gel using a gradient of 0-100% ethyl acetate in hexane to provide the desired product (17 mg, 35%) as a light yellow waxy solid. 1H NMR (CDCl3): delta 8.71 (d, J = 4.9 Hz, 1H), 8.12 (d, J = 8.1 Hz, 1H), 7.93 (dd, J = 15.8 Hz, 2.0 Hz, 1H), 7.68 (dd, J = 7.6, 1.8 Hz, 1H), 7.56 (dd, J = 8.0, 4.6 Hz, 1H), 7.55 (d, J = 7.4 Hz, 1H), 7.54 (dt, J = 7.4, 1.9 Hz, 1H), 7.36 (d, J = 15,8 Hz, 1H), 7.09 (t, J = 7.6, 1H), 7.03 (d, J = 8.2 Hz, 1H), 3.93 (s, 3H). 13C NMR (CDCl3) delta 190.8, 157.3, 148.2, 147.1, 145.2, 136.5, 135.1, 134.4, 132.6, 131.6, 129.7, 129.6, 127.2, 125.5, 120.0, 110.6, 54.7. HRMS (FAB): calcd C16H12F3NO2 + H = 308.0898, found 308.0889.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5352 - 5359

Yield	Reaction Conditions	Operation in experiment
	With manganese(IV) oxide; In dichloromethane; for 4h;Reflux;	General procedure: Prepared from (2- trifluoromethyl-pyridin-3-yl)-methanol (0.05 g, 0.28 mmol), manganese dioxide (0.7 g, 8.0 mmol) and anhydrous dichloromethane (10 mL) using the procedure described for Example 7, Step 1. The desired product was isolated as a yellow oil (0.035 g, 71% yield) by concentration of the filtrate on a rotary evaporator and used without further purification. 1H-NMR (400MZ, CDCI3) delta 10.40 (1H, s), 8.83 (1H, d, J=4.7 Hz), 8.37 (1H, d, J=8.0 Hz), 7.63 (1H, dd, J = 8.0 and 4.7 Hz).

18
[ 116308-35-1 ]
ethyl 1-(2-(4-(2-amino-4-(ethoxycarbonyl)phenyl)piperazin-1-yl)ethyl)-2-(2-(trifluoromethyl)pyridin-3-yl)-1H-benzo[d]imidazole-5-carboxylate [ No CAS ]

Reference： [1]Letters in drug design and discovery,2016,vol. 13,p. 691 - 696
[2]Letters in drug design and discovery,2016,vol. 13,p. 691 - 696

19
[ 116308-35-1 ]
C₇H₅F₃NO₄S^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium metabisulfite; water; In ethanol; at 20℃; for 1h;	General procedure: The appropriate substituted pyridine aldehyde (10 mmol) was dissolved in ethanol (20 mL) and sodium metabisulfite (15 mmol) in 5 mL water was added in portion over 5 minutes.The reaction mixture was stirred at room temperature for 1 h, and subsequently stirred at 4oC overnight and the formed precipitate was filtered and dried to get sodium bisulfite adducts.
	With sodium hydrogensulfite; In ethanol; water; at 4 - 20℃;	General procedure: The appropriate substituted pyridine aldehyde (10 mmol) was dissolved in ethanol (20 mL) and sodium metabisulfite (15 mmol) in 5 mL water was added in portion over 5 minutes. The reaction mixture was stirred at room temperature for 1 h, and subsequently stirred at 4C overnight and the formed precipitate was filtered and dried to get sodium bisulfite adducts.

Reference： [1]Letters in drug design and discovery,2016,vol. 13,p. 691 - 696
[2]Letters in drug design and discovery,2016,vol. 13,p. 691 - 696

20
[ 623-33-6 ]
[ 116308-35-1 ]
(E)-ethyl 2-(((2-(trifluoromethyl)pyridin-3-yl)methylene)amino)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%		Ethyl 2-aminoacetate hydrochloride (3.49 g, 24.98 mmol) and magnesium sulfate (4.81 g, 40.0 mmol) were suspended in dichloromethane (33.3 mL) and the suspension was treated with triethylamine (3.48 mL, 24.98 mmol). After 1 hour, <strong>[116308-35-1]2-(trifluoromethyl)nicotinaldehyde</strong> (3.5 g, 19.99 mmol) in dichloromethane (5 mL) was added and the reaction mixture was stirred at room temperature for 16 hours. The solid material was removed via filtration and the filtrate was washed with water and brine, dried over sodium sulfate, filtered, and concentrated to provide (E)-ethyl 2-(((2-(trifluoromethyl)pyridin-3-yl)methylene)amino)acetate (5.08 g, 19.52 mmol, 98% yield), which was used without further purification. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.80 (dd, J=4.6, 1.6 Hz, 1H), 8.68 (td, J=2.5, 1.4 Hz, 1H), 8.62-8.45 (m, 1H), 7.87-7.62 (m, 1H), 4.56 (d, J=1.3 Hz, 2H), 4.13 (m, 2H), 1.19 (m, 3H); MS (ESI+) m/z 261.0 (M+H)+.
98%		(E)-ethyl 2-(((2-(trifluoromethyl)pyridin-3-yl)methylene)amino)acetate Ethyl 2-aminoacetate hydrochloride (3.49 g, 24.98 mmol) and magnesium sulfate (4.81 g, 40.0 mmol) were suspended in dichloromethane (33.3 mL) and the suspension was treated with triethylamine (3.48 mL, 24.98 mmol). After 1 hour, <strong>[116308-35-1]2-(trifluoromethyl)nicotinaldehyde</strong> (3.5 g, 19.99 mmol) in dichloromethane (5 mL) was added and the reaction mixture was stirred at room temperature for 16 hours. The solid material was removed via filtration and the filtrate was washed with water and brine, dried over sodium sulfate, filtered, and concentrated to provide (E)-ethyl 2-(((2-(trifluoromethyl)pyridin-3-yl)methylene)amino)acetate (5.08 g, 19.52 mmol, 98% yield), which was used without further purification. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.80 (dd, J=4.6, 1.6 Hz, 1H), 8.68 (td, J=2.5, 1.4 Hz, 1H), 8.62-8.45 (m, 1H), 7.87-7.62 (m, 1H), 4.56 (d, J=1.3 Hz, 2H), 4.13 (m, 2H), 1.19 (m, 3H). MS (ESI+) m/z 261.0 (M+H)+.

Reference： [1]Patent: US2018/99931,2018,A1 .Location in patent: Paragraph 2103
[2]Patent: US2018/99932,2018,A1 .Location in patent: Paragraph 1563

21
[ 116308-35-1 ]
(2S,3R,4S,5S)-ethyl 3-(tert-butyl)-4-nitro-5-(2-(trifluoromethyl)pyridin-3-yl)pyrrolidine-2-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/99931,2018,A1

22
[ 116308-35-1 ]
(2S,3R,4S,5S)-ethyl 3-(tert-butyl)-4-nitro-5-(2-(trifluoromethyl)pyridin-3-yl)pyrrolidine-2-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/99932,2018,A1

23
[ 116308-35-1 ]
2-(trifluoromethyl)nicotinaldehyde oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine; hydroxylamine hydrochloride; at 20℃; for 1h;	A solution of <strong>[116308-35-1]2-(trifluoromethyl)nicotinaldehyde</strong> (1.96 g, 11.19 mmol) and hydroxylamine hydrochloride (0.856 g, 12.31 mmol) in pyridine (6 mL) was stirred at rt for 1 h. Pyridine was removed under vacuum to give the desired product (2.12 g, 100%) as a white solid: LCMS (ES): m/z 191.0 [M+H]+.

Reference： [1]Patent: WO2019/89665,2019,A1 .Location in patent: Page/Page column 61

24
[ 116308-35-1 ]
C₇H₄ClF₃N₂O [ No CAS ]